WO1996002523A1

WO1996002523A1 - Herbicidal arylimino-substituted triazoles, thiadiazoles or oxadiazoles

Info

Publication number: WO1996002523A1
Application number: PCT/EP1995/002547
Authority: WO
Inventors: Otto Schallner; Andreas Lender; Hans-Joachim Santel; Markus Dollinger
Original assignee: Bayer Aktiengesellschaft
Priority date: 1994-07-14
Filing date: 1995-06-30
Publication date: 1996-02-01
Also published as: US5767041A; EP0770069A1; JPH10504538A; DE4424787A1; AU2979595A

Abstract

The invention concerns novel substituted aryliminoheterocyclic rings of the general formula (I), (I), in which A stands for oxygen, sulphur or the grouping N-R1, wherein R1 stands for hydrogen or in each case optionally substituted alkyl, alkenyl or alkinyl, E stands for the grouping (a) or (b), wherein Q stands for oxygen, sulphur or the grouping N-R1 (R1 having the above meaning), R2 stands for hydrogen, cyano or in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkenyl, R stands for hydrogen or in each case optionally substituted alkyl, alkenyl or alkinyl, and Ar stands for in each case optionally substituted monocyclic or bicyclic aryl or heteroaryl. The invention further concerns a process for their preparation and their use as herbicides.

Description

HERBICIDAL ARYLIMINO-SUBSTITUTED TRIAZOLE, THIADIAZOLE OR QXADIAZOLE

The invention relates to new substituted aryliminoheterocycles, processes for their preparation and their use as herbicides.

Substituted aryliminoheterocycles have so far not been known as biologically active substances.

The new substituted aryliminoheterocycles of the general formula (I) have now been found

EN ^' ^{A _} ^ Ar

in which

A stands for oxygen, sulfur or the grouping N-R ^, where

R stands for hydrogen or for optionally substituted alkyl, alkenyl or alkynyl,

E represents one of the groupings below,

in which

Q represents oxygen, sulfur or the grouping NR.1 (where Rl has the meaning given above) and R ^{2 represents} hydrogen, cyano or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl,

R stands for hydrogen or for optionally substituted alkyl, alkenyl or alkynyl, and

Ar represents in each case optionally substituted, monocyclic or bicyclic aryl or heteroaryl.

The general formula (I) thus stands for the isomeric compounds of the general formulas (IA) and (D3) below.

(IA) dB)

The new substituted arylimino heterocycles of the general formula (I) are obtained if arylimino compounds of the general formula (II)

^ Ar CD

I H in which

A, R_ R and Ar have the meanings given above,

- and / or tautomeric compounds for this purpose -

with reactive carbonic acid derivatives of the general formula (III) T OH) x in which

Q has the meaning given above and

X represents halogen, alkoxy, aryloxy or aralkoxy,

optionally cyclized in the presence of a reaction auxiliary and optionally in the presence of a diluent

and optionally the compounds of the formulas (IA) and / or (EB) obtained in this case, in the event that R ² in this case represents hydrogen, with alkylating agents of the general formula (IV)

R2-X ¹ (IV)

in which

R ² has the meaning given above with the exception of hydrogen and

X 'represents halogen or the grouping -O-SO2-OR ² ,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

The new substituted aryliminoheterocycles of the general formula (I) are notable for strong herbicidal activity.

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl, are each straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine. The invention preferably relates to compounds of the formula (I) in which

A for oxygen, sulfur or the grouping N-R! stands, where

Rl for hydrogen or for optionally substituted by cyano, halogen, C1-C4-alkoxy, -CC-C4-alkyl-carbonyl or C] -C4-alkoxy-carbonyl-alkyl having 1 to 6 carbon atoms or for each optionally substituted by halogen alkenyl or alkynyl each having 2 to 6 carbon atoms,

E represents one of the groupings below,

R ² R ²

in which

Q represents oxygen, sulfur or the grouping N-R-- (where R ^ has the meaning given above as preferred) and

R ^{2 represents} hydrogen, cyano or optionally substituted by cyano, halogen, C 1 -C 4 alkoxy, C 1 -C 4 alkyl carbonyl or C 4 -C 4 alkoxy carbonyl alkyl having 1 to 6 carbon atoms or for each in each case is optionally substituted by halogen-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms or by cycloalkyl having 3 to 6 carbon atoms or cycloalkenyl having 5 or 6 carbon atoms which is optionally substituted by halogen or C 1 -C 4 -alkyl,

R for hydrogen or for optionally by cyano, halogen, C1-C4-

Alkoxy, C _] -C4 alkyl carbonyl or C] -C4 alkoxy carbonyl substituted

Alkyl with 1 to 6 carbon atoms or for each optionally by

Halogen substituted alkenyl or alkynyl each having 2 to 6 carbon atoms, and Ar represents one of the following, optionally substituted, monocyclic or bicyclic aryl or heteroaryl groups,

wherein

R ^{3 represents} hydrogen or halogen,

R ^ represents hydrogen, cyano, nitro, thiocarbamoyl, halogen or C 1 -C 4 -alkyl or C1-C4-alkoxy which is optionally substituted by halogen,

R ^ represents the grouping below,

-A * -A ² -A ³

in which

.A.1 for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ^ -, wherein A ^{4 is} hydrogen, hydroxy, C1-C4- alkyl, Cι-C4 -Alkoxy, phenyl, C] -C ₄ -alkylsulfonyl or phenylsulfonyl, or

A * further for each optionally substituted by fluorine, chlorine or bromine, Cj-Cό-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-Cö-alkynediyl, C3-C6-cycloalk.1nd.yl, C3 -Cö-cycloalkenediyl or phenylene,

A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁴ -, where A ^{4 represents} hydrogen, hydroxy,

C1-C4- alkyl, -CC ₄ alkoxy, phenyl, C j -C ₄ alkylsulfonyl or phenylsulfonyl, or A ² furthermore for C 1 -C 6 -alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenediyl, C2-Cό-alkynediyl, C3-C C2-cycloalkanediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl, in each case optionally substituted by fluorine, chlorine or bromine or phenylene,

A ³ for hydrogen, hydroxy, amino, cyano, isocyano, thiocyanato, nitro,

Carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl, each with 1 in each case optionally substituted by halogen or C 1 -C 4 -alkoxy to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen-substituted alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, each for optionally by Halogen, cyano, carboxy, Cj-C4-alkyl and / or C1-C4-alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or f for each optionally by nitro, cyano, carboxy,

Halogen C _] -C4-alkyl, Cι-C4-haloalkyl, C1-C4-A.ky.oxy, C] -C - haloalkyloxy and / or Cι-C4-alkoxy-carbonyl substituted phenyl, phenyloxy, phenyl-C -C4 alkyl, phenyl-C1-C4-alkoxy, phenyloxycarbonyl or phenyl-C1-C4-alkoxycarbonyl, (in each case optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl,

Thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C \ -C4-alkyl, furyl-C _] -C ₄ -alkyl, thienyl-C \ -C4-al yl , Oxazolyl-C] -C4-alkyl, isoxazole-Cj-C -alkyl, thiazole-C] -C -alkyl, pyridinyl-C] -C -alkyl, pyrimidinyl-C - C4-alkyl, pyrazolylmethoxy, furylmethoxy, for perhydropyranylmethoxy or pyridyl ethoxy,

R ^{6 represents} hydrogen or halogen, R? is hydrogen, hydroxy, optionally substituted by cyano, halogen, C _j - C4 alkoxy, Cι-C4-alkyl-carbonyl or Cι-C4-alkoxy-carbonyl substitu¬ iertes alkyl having 1 to 6 carbon atoms, represents in each case optionally substituted by halogen Alkenyl or alkynyl each having 2 to 6 carbon atoms, each optionally by halogen or C \ -

C4-Alkyl substituted cycloalkyl or cycloalkylalkyl, each having 3 to 6 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, for alkoxy or alkenyloxy optionally substituted by halogen, each having up to 6 carbon atoms, or for each optionally by cyano, halogen, C1-C4-

Alkyl, -C-C4-haloalkyl, C1-C4-alkoxy or -CC-C4-haloalkoxy substituted benzyl or benzyloxy, and

G represents one of the groups below,

-O-CO-, -S-CO-, -OC (R ⁸ , R ⁹ ) -CO-, -C (R ⁸ , R ⁹ ) -O-CO-, -C (R ⁸ , R ⁹ ) - C (R ⁸ , R ⁹ ) -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CO-, -C (R ⁸ ) = C (R ⁸ ) -, -C (R ⁸ ) = C (R ⁸ ) -

CO-, -C (R ⁸ , R ⁹ ) -CO-, -N (Rl °) -C (R ⁸ ; R ⁹ ) -CO-, -C (R ⁸ ) = N-, -O-CO- C (R ⁸ , R ⁹ ) -

in which

R ⁸ and R ^{9 are the} same or different and individually represent hydrogen or alkyl having 1 to 6 carbon atoms or together for

Alkanediyl having 2 to 6 carbon atoms, and

RIO represents hydrogen or alkyl having 1 to 6 carbon atoms.

The invention relates in particular to compounds of the formula (I) in which

represents oxygen, sulfur or the grouping N-R ^, where

K- for hydrogen or for each optionally by cyano, fluorine,

Chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine,

represents one of the groups below,

in which

Q represents oxygen, sulfur or the grouping N-Rl (where R has the meaning given above as being particularly preferred) and

R ^{2 represents} hydrogen, cyano or methyl, ethyl, n- or i-propyl, n-, i-, s- or t- optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl Butyl, or propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine, chlorine or bromine, or cyclopentenyl or cyclohexenyl,

R represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, or represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine, chlorine or bromine, and

Ar represents one of the following, optionally substituted, monocyclic or bicyclic aryl or heteroaryl groups,

wherein

R ^{3 represents} hydrogen, fluorine or chlorine, R ^{4 represents} hydrogen, cyano, chlorine, bromine, methyl or trifluoromethyl,

R5 represents the grouping below,

-A! -A ² -A ³

in which

A ^{1 represents} a single bond, represents oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, Methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl, or

A ¹ furthermore for methylene, ethane-l, l-diyl, ethane-l, 2-diyl, propane-l, l-diyl, propane-l, 2-diyl, propane-l, 3-diyl, ethene-l, 2-diyl, propene-1,2-diyl,

Propene-1,3-diyl, ethine-1,2-diyl or propine-1,3-diyl,

Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl, or

A ² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,

A ³ for hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl,

Sulfo, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, substituted by fluorine, chlorine, methoxy or ethoxy, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl,

Ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxy- carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl, for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butylidenylamino, butylenylamino, each optionally substituted by fluorine or chlorine , Propenyloxycarbonyl,

Butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, for cyclopropyl, in each case optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl , Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy,

Cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo-propyl-methoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino, cyclohexylidenamino, cyclylentyloxyoxyyl, cyclylentyloxyoxyoxy, cyclylentyloxyoxyyl, cyclylentyloxyoxycarbonyl, cyclylentyloxyoxycarbonyl, cyclylentyloxyoxycarbonyl, cyclylentyloxycarbonyl, , Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy, benzyl , Phenylethyl, benzyloxy, phenyloxycarbonyl,

Benzyloxycarbonyl, (in each case wholly or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethylmolylyl, oxyl Isoxazole methyl, thiazole methyl, pyridinyl methyl,

Pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy,

R ^{6 represents} hydrogen, fluorine or chlorine,

^~ for hydrogen, hydroxy, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or

Ethoxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally with fluorine, chlorine or bromine substituted propenyl, butenyl, propynyl or butynyl, each for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by fluorine and / or chlorine, optionally substituted by fluorine, chlorine, bromine, methyl or ethyl Methoxy,

Ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy, or for each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy Is benzyl or benzyloxy, and

G represents one of the groups below,

-O-CO-, -S-CO-, -OC (R ⁸ , R ⁹ ) -CO-, -C (R ⁸ , R ⁹ ) -O-CO-, -C (R ⁸ , R ⁹ ) - C (R ⁸ , R ⁹ ) -, -C (R ⁸ ) = C (R ⁸ ) -, -C (R ⁸ , R ⁹ ) -CO-, -N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CO-, -C (R ⁸ ) = N-, -O-CO-C (R ⁸ , R ⁹ ) -

in which

R ⁸ and R ^{9 are the} same or different and are individually hydrogen, methyl,

Ethyl, n- or i-propyl or together represent ethane-1,2-diyl, and

RI ^{Q represents} hydrogen, methyl, ethyl, n- or i-propyl.

The general definitions given above or those specified in preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediate products required in each case for the preparation. These radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds.

Examples of the possible combinations of the groups A, Q, R, K and Ar defined above are listed below: RR ² ar

RR ² ar

CH

CH

QRR ² ares

CH_ RR ² ar

CH, RR ² ar

QRR ² ares

0-CH _, - C≡CH QRR ² ares

0-CH ₂ -C≡CH RR ² ar

0- (CH ₂ CH ₂ 0) ₂ -CH ₃ QRR ² ares

0- (CH ₂ CH ₂ 0) ₂ -CH ₃ RR ² ar

0- (CH ₂ CH 2 ₂ 0 ~~ ') / 2 _? -CK

0- (CH ₂ CH ₂ 0) ₂ -CH RR ² ar

RR ² ar

QRR ² ares

RR ² ar

RR ² ar

RR ² ar

RR ² ar

RR ² ar

RR ² ar

OC ₂ H ₅

RR ² ar

RR ² ar

RR ² ar

RR ² ar

CH ₂ -C≡CH RR ² ar

RR ² ar

RR ² ar

RR ² ar

RR ² ar

RR ² ar

CH, -C≡CH RR ² ar

RR ² ar

RR ² ar

RR ² ar

RR ² ar

RR ² ar

RR ² ar

CH

RR ² ar

CH ₂ -CH ₂ -COOC ₂ H ₅ R ² ar

O CH ₃ CF ₃

*> -

CH ₂ -CH ₂ -COOC ₂ H ₅

CH = CH-COOC ₂ H ₅ RR ² ar

CH = CH-COOC ₂ H ₅ RR ² ar

OCH ₂ -COOC ₂ H ₅ RR ² ar

SCH ₂ -COOC ₂ H ₅ RR ² ar

RR ² ar

O CH C ₂ H ₅ -ΪL ^~ - OCH-C≡CH

I CH,

CH, RR ² ar

OCH "-C≡CH QRR ² ares

NH-S0 ₂ C ₂ H ₅ RR ² ar

NH-S0 ₂ C ₂ H ₅ RR ² ar

NH-S0 ₂ C ₃ H ₇ RR ² ar

OCH ₂ CH ₂ OCH ₃ RR ² ar

OCH ₂ CH ₂ OCH ₃ RR ² ar

OCH ₂ CH ₂ OCH ₃ QRR ² ares

OCH (CH ₃ 3) ' ₂ RR ² ar

OCH (CH ₃ ) ₂ RR ² ar

RR ² ar

RR ² ar

OCH ₂ -CH ₂ -OCH ₃ RR ² ar

H ₂ -OCH ₃

If, for example, 4- (4-chloro-2-fluoro-5-methoxy-phenyl) -2-methyl-thiosemicarbazide and phosgene are used as starting materials and chlorodifluoromethane in the subsequent stage as an alkylating agent, the course of the reaction in the process according to the invention can be carried out the following formula scheme are outlined:

Formula (II) provides a general definition of the arylimino compounds to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I). In the formula (II), A, R, R ² and Ar preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for A, R , R ² and Ar were specified.

The starting materials of the formula (II) are known and / or can be prepared by known processes (cf. EP-A 258182, US-P 4721522, DE-A 3722074, US-P 5108486, production examples).

Formula (III) provides a general definition of the reactive carbonic acid derivatives to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I). In formula (III), Q preferably or in particular has the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Q; X preferably represents fluorine. Chlorine, bromine, C i -C4 alkoxy, phenoxy or benzyloxy, especially for chlorine. Methoxy or phenoxy. The starting materials of the formula (III) are known synthetic chemicals.

Formula (IV) provides a general definition of the alkylating agents which may be used further as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I). In formula (IV), R ² preferably or in particular has the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R ² ; χl is preferably chlorine, bromine, iodine or the grouping -O-SO ₂ -OR ² .

The starting materials of the formula (IV) are known synthetic chemicals.

The usual organic solvents are suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetrachloromethane; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; A ide, such as N.N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The process according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. All conventional inorganic or organic bases are suitable as such. These include, for example, alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, lithium, sodium, potassium or calcium hydride. Lithium, sodium or potassium amide, sodium or potassium methylate, sodium or potassium ethylate, sodium or potassium propylate, aluminum iso- propylate, sodium or potassium tert-butoxide, sodium or potassium hydroxide, ammonium hydroxide, sodium, potassium or calcium acetate, ammonium acetate, sodium, potassium or calcium carbonate, ammonium carbonate, sodium or potassium hydrogen carbonate , and basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, NN-dimethylcyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, 2-methyl -, 3-methyl- and 4-methyl-pyridine, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl- pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclo-octane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -10 C and +150 C, preferably at temperatures between 0 C and 100 C, especially at temperatures between 10 ° C and 80C. The process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar

To carry out the process according to the invention, the starting materials required in each case are generally used in approximately aquimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess. The reactions are generally carried out in a suitable diluent, if appropriate in the presence of a reaction auxiliary, and the reaction mixture is required for several hours in each case Temperature stirred In the process according to the invention, the workup is carried out in each case by customary methods (cf. the preparation examples).

The active compounds according to the invention can be used as defoliants, desiccants, herbicides and in particular as weed killers. Weeds in the broadest sense are to be understood as all plants which grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends depends essentially on the amount applied The active compounds according to the invention can be used, for example, in the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Sonusum, Carduus , Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sor¬ ghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittirpum, Eleocharis, Pas , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants

Depending on the concentration, the compounds are suitable for total weed control, for example on industrial and track systems and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forest, ornamental wood, fruit, wine , Citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective weed control in annual crops The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, loose powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric fabrics

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents

If water is used as an extender, it is also possible, for example, to use organic solvents as auxiliary solvents. Liquid solvents are essentially suitable. Aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water

Solid carrier materials are suitable

Eg ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz. Attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, as solid carrier materials for granules are suitable, for example, broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules inorganic and organic flours as well as granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, emulsifiers and / or foam-producing agents are possible, for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene Fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; The following may be used as dispersants: for example ligin sulfite waste liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids such as dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as, for example, 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chloropropham, desmedipham, phenmedipham and propham; Chloroacetanilides, such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor: dinitroanilines, such as, for example, oryzalin, pendimethalin and trifluralin; Diphenyl ethers such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas such as chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines such as alloxydim, clethodim, cycloxvdim, sethoxydim and tralkoxydim; Imidazolinones, such as imazethapyr, Imazamethabenz, imazapyr and imazaquin; Nitriles such as bromoxynil, dichlobenil and ioxynil; Oxyacetamides such as mefenacet; Sulfonylureas, such as, for example, amidosulfon, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as butylates, cycloates, dialates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines, such as, for example, atrazine, cyanazine, simazine, simetryne, terbutryne and terbutyl azine; Triazinones such as hexazmon, metamitron and metribuzin; Others, such as, for example, aminotriazole, Benfüresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofümesate, Fluorochloridoue, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below. Manufacturing examples:

example 1

To a suspension of 3.1 g (10 mmol) of 2-methyl-4- (7-fluoro-3,4-dihydro-3-oxo-4-propargyl- (2H) -l, 4-benzoxazin-6-yl ) -thiosemicarbazid in 50 ml dichloromethane is given at 20 C 6 g (12 mmol) of a 20% solution of phosgene in toluene. The reaction mixture is heated to 40 ° C. for about 15 hours, the solvent is removed in vacuo and the residue is taken up in water. It is neutralized with sodium bicarbonate solution, the solid is filtered off, washed with water and dried in vacuo at 40-50 C.

2.8 g (84% of theory) of 2- (7-fluoro-3,4-dihydro-3-oxo-4-propargyl- (2H) -1,4-benzoxazin-6-yl-imino) are obtained. 3-methyl-3,4-dihydro-5-oxo (4H) -1,3,4-thiadiazole. Melting point: 214 C.

Example 2

To a mixture of 1.7 g (5 mmol) of 2- (7-fluoro-3,4-dihydro-3-oxo-4-propargyl- (2H) - 1, 4-benzoxazin-6-yl-imino) - 3-methyl-3,4-dihydro-5-oxo- (4H) -1,3,4-thiadiazole, 1.4 g (10 mmol) of potassium carbonate and 50 ml of acetonitrile are added to 1.1 g (7.5 mmol) ) Methyl iodide. The reaction mixture is heated to 40 C for 5 hours. The solvent is removed in vacuo, the residue is taken up in water, neutralized and extracted with dichloromethane. The organic phase is dried over magnesium sulfate, concentrated and purified by chromatography (eluent: dichloromethane / methanol: 40: 1).

0.75 g (42% of theory) of 3,4-dimethyl-2- (7-fluoro-3,4-dihydro-3-oxo-4-prop-_rgyl- (2H) -l _J 4-benzoxazine is obtained -6-yl-imino) -3,4-dihydro-5-oxo-l, 3,4-thiadiazole. Melting point: 104 C.

Example 3

To a solution of 3.3 g (11 mmol) of 2- (4-chloro-2-fluoro-5-ethoxy-phenyl-imino) -3-methyl-3,4-dihydro-5-oxo (4H) - 1,3,4-thiadiazole in 80 ml of dimethylformamide is added to 3.4 g (24 mmol) of potassium carbonate and chlorodifluoromethane is slowly introduced at 60 ° C. in the course of 6 hours. After the reaction has ended, the majority of the solvent is removed in vacuo. The oily residue is taken up in water, neutralized with hydrochloric acid and extracted with dichloromethane. The organic phase is dried over magnesium sulfate, concentrated and separated by chromatography with dichloromethane as the eluent.

The first fraction obtained is 0.4 g of 2- (4-chloro-2-fluoro-5-ethoxyphenylimino) -4-di-fluoromethyl-3-methyl-3,4-dihydro-5-oxo-l, 3,4 thiadiazole. Melting point: 121 C.

The second fraction obtained is 0.5 g of 2- (4-chloro-2-fluoro-5-ethoxyphenylimino) -3-methyl-5-difluoromethoxy-l, 3,4-thiadiazole. Melting point: 42 C.

F., The compound listed in Table 1 as Example 45 can be produced, for example, as follows:

0.66 g is added to a solution of 1.7 g (5.7 mmol) of 4- (4-cyano-2-fluoro-5-i-propoxy-phenyl) -1, 2-dimethylthiosemicarbazide in 30 ml of dry dichloromethane (5.7 mmol) thiophosgene. The reaction is slightly exothermic. The reaction mixture is stirred for 4 hours at reflux temperature, the solvent is removed in vacuo and the residue is stirred with saturated sodium bicarbonate solution. The solid formed is suctioned off, washed with water and pressed onto clay.

1.5 g (78% of theory) of 2- (4-cyano-2-fluoro-5-i-propoxy-phenylimino) -3,4-dimethyl-5-thio-l, 3,4-thiadiazole of Melting point 117 C.

Analogously to Examples 1 to 3 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) - or of the formulas (IA) and (FB) - listed in Table 1 below.

Table 1: Examples of the compounds of the formula (I)

Example - general Ar RR ² melting no. For point mel (C)

CHX≡CH

sp- allg. Ar RR ² Melting No. For point mel (C)

CH ₃ CH ₃ OS (amorphous)

OCH (CH ₃ ) ₂ For example Ar RR ² Melting No. For point mel (C)

O ^/ OC ₂ H ₅

CN

30 IA CH ₃ HO 161

For example Ar RR ² Melting No. For point mel (C)

sp- general Ar ² Melting No. For point mel (C)

CH ₃ CH ₃ OS (amorphous)

H ₅

41 IB CH ₃ CHF ₂ OS (amorphous)

sp- general Ar RR ² QA Melting No. For point mel (C)

Example - general Ar RR ² Schmelz¬

No. For¬punkt mel (C)

For example Ar RR ² Melting No. For point mel (C)

CHXH = CH,

sp- general Ar ² Melting No. For point mel (C)

58 IA CH ₃ CHF ₂ O

CH ₂ C≡CH

sp - general Ar RR ² Melting No. For¬punkt mel (C)

63 IA O S (amorphous)

64 CH ₃ -CH ₂ CH≡CH ₂ OS (amorphous)

CN

65 IB <P CH ₃ CHF ₂ OS (amoφh)

66 m CH ₃ CHF OS (amorphous)

sp - general Ar RR ² melting. No. For¬punkt mel (C)

67 IA CH ₃ CH ₃ OS (amorphous)

68 IA CH ₃ CH ₃ OS (amorphous)

R ² melting point (C)

Ingredients of the formula (part:

Example (II- 1)

1st stage

26.4 g (0.12 mol) 6-A are added to a mixture of 12 g (0.12 mol) calcium carbonate, 150 ml water, 13.7 g (0.12 mol) thiophosgene and 100 ml dichloromethane with stirring -___ ino-7-fluoro-3,4-dihydro-3-oxo-4-prop__rgyl- (2H) -l, 4-beι_zoxazin in 50 ml dichloromethane. The reaction mixture is stirred at 35 C to 40 C for about 3 hours. Then, after filtration, the organic phase is separated off, dried with magnesium sulfate and filtered. The filtrate is freed from the solvent in vacuo.

27 g (85.9% of theory) of 6-isothiocyanato-7-fluoro-3,4-dihydro-3-oxo-4-propargyl- (2H) -1,4-benzoxazine are obtained. Melting point: 128 C.

2nd stage

A solution of 5.24 g (20 mmol) of 6-isothiocyanato-7-fluoro-3,4-dihydro-3-oxo-4-propargyl- (2H) -l, 4-benzoxazine in 60 ml of tetrahydrofuran is added 5 C to IO C 0.92 g (20 mmol) methyl hydrazine. After stirring at IO C for two hours, the solvent is removed in vacuo and the solid residue is recrystallized from isopropanol.

4.7 g (76.3% of theory) of 2-methyl-4- (7-fluoro-3,4-dihydro-3-oxo-4-propargyl- (2H) -1,4-benzoxazin-6 are obtained -yl) thiosemicarbazide. Melting point '162 C. Analogously to Example (II-1), it is also possible, for example, to prepare the compounds of the formula (II) listed in Table 2 below - and / or tautomers thereof.

Table 2: Examples of the compounds of the formula (II)

Example - Ar R ² A melting point (C)

sp- Ar RR ² A melting point (C)

sp- Ar RR ² Schmelz¬

No. point (C)

Example Ar RR ² melting point (C)

Examples of use:

Example A

Post emergence test

Solvent: 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants with a height of 5 - 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

Example B

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Seeds of the test plants are sown in normal soil and watered with the active ingredient preparation after 24 hours. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

0% = no effect (like untreated control) 100% = total destruction

Table A

Post emergence test / greenhouse

Active ingredient effort- wheat Abutilon Amaran- Datura Ipomoea Sola- Viola amount thus num g ha

5 30 10 100 100 100 100 100 100

6 30 5 95 100 100 100 100 100

2 30 20 100 100 100 100 100 100

8 30 20 100 100 100 100 100 100

Table B

Pre-emergence test / greenhouse

Active ingredient expenditure- Barley Abutilon Cheno- Galin-Matri- Portu-Sol quantity podium soga caria laca num g / ha

5 125 10 100 95 90 100 100 100

6 60 20 95 100 80 70 95 95

2 125 10 100 100 100 100 100 100

8 125 10 100 100 100 100 100 100

3 125 0 100 100 100 95 100 100

Claims

claims

1. Substituted aryliminoheterocycles of the general formula (I)

R

EN ^'

AA ^(l)

in which

A represents oxygen, sulfur or the grouping N-R ^, where

R ^{1 represents} hydrogen or represents optionally substituted alkyl, alkenyl or alkynyl,

E represents one of the groupings below,

N.

'^ ^

in which

Q represents oxygen, sulfur or the grouping NR ¹ (where R ^{1 has} the meaning given above) and

R ^{2 represents} hydrogen, cyano or optionally substituted in each case

Alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl,

Ar represents in each case optionally substituted, monocychic or bicyclic aryl or heteroaryl. Substituted aryliminoheterocycles of the general formula (I) according to Claim 1, characterized in that

A represents oxygen, sulfur or the grouping NR ¹ , where

R represents hydrogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonyl or C 1 -C 6 -alkoxycarbonyl or for alkenyl or alkynyl which is optionally substituted by halogen each represents 2 to 6 carbon atoms,

E represents one of the groupings below,

^Q ^ / ^N - N. ^

in which

Q represents oxygen, sulfur or the grouping NR ¹ (where R ^{1 has} the meaning given above as preferred) and

R ^{2 represents} hydrogen, cyano or alkyl optionally substituted by cyano, halogen, C1-C4-alkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl having 1 to 6 carbon atoms or each optionally substituted by halogen Alkenyl or alkynyl each having 2 to 6 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms or cycloalkenyl having 5 or 6 carbon atoms which is optionally substituted by halogen or C 1 -C 4 -alkyl,

R represents hydrogen or alkyl optionally substituted by cyano, halogen, C1 -C4 alkoxy, C1 -C4 alkyl carbonyl or C1 -C4 alkoxycarbonyl alkyl having 1 to 6 carbon atoms or each optionally halogen-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms, and

represents one of the following, optionally substituted, monocyclic or bicyclic aryl or heteroaryl groups,

woπn

R ^ represents hydrogen or halogen,

R ^{4 represents} hydrogen, cyano, nitro, thiocarbamoyl, halogen or represents in each case optionally substituted by halogen C _] -C4-alkyl or Cj-C4-alkoxy,

R ^ represents the grouping below,

-A ^] -A ² -A ³

in which

A ¹ for a single bond, for oxygen, sulfur, -SO-, -SO ₂ τ, -

CO- or the grouping -NA ⁴ -, wherein A ^{4 is} hydrogen, hydroxy, C i -C ₄ alkyl, C j -C ₄ alkoxy, phenyl, C _] -C alkyl sulfonyl or phenyl sulfonyl , or

A ¹ also for each optionally substituted by fluorine, chlorine or bromine, Cj-Cό-alkanediyl, C ₂ -C6 -alkenediyl, C ₂ -Cö-azaalkenediyl, C ₂ -C6-alkynediyl, C ₃ -C6-cycloalkanediyl, C ₃ -C6-cycloalkenediyl or phenylene,

A ^{2 stands} for a single bond, for oxygen, sulfur, -SO-, -SO -, - CO- or the grouping -NA ⁴ -, where A ^{4 stands} for water substance, hydroxy, C] -C ₄ alkyl, C ₁ -C ₄ alkoxy, phenyl, C ₁ -C ₄ alkyl sulfonyl or phenyl sulfonyl, or

A ² for Ci-Cg-alkanediyl, C ₂ -C6-alkenediyl, C ₂ -C6-azaalkenediyl, C ₂ -C6-alkynediyl, C ₃ -C6-cycloalkanediyl, C ₃ each also optionally substituted by fluorine, chlorine or bromine ₃ -C6-cycloalkenediyl or phenylene,

A ³ for hydrogen, hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl which is optionally substituted by halogen or C1-C4alkoxy sulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy- (thio) phosphoryl, each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or optionally substituted by halogen

Alkynyloxycarbonyl, each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, for cycloalkyl, cycloalkyloxy substituted by halogen, cyano, carboxy, C 1 -C 4 -alkyl and / or C 1 -C 4 -alkoxycarbonyl, if appropriate Cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for each case optionally by nitro, cyano, carboxy, halogen C1-C4-alkyl, Cι-C4-haloalkyl, C] -C4-alkyloxy, C \ -C4-haloalkyloxy and / or C _j -C4-alkoxy-carbonyl substituted phenyl, phenyloxy, phenyl-C 1-C.4-a.kyl, phenyl- C \ -C4-alkoxy, phenyloxycarbonyl or phenyl-C _] -C4-alkoxycarbonyl, (each optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, Thiadiazolyl , Pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C _] -C ₄ -alkyl, furyl -CC-C ₄ -all-yl, thienyl-C] -C ₄ -alkyl, oxazolyl- -C-C4-alkyl, isoxazole-Cι-C4-al__yl, thiazole-Cι-C4-alkyl, pyridinyl-C -C4-alkyl, pyrimidinyl-Cι-C4-alkyl, pyrazolylmethoxy, furyl methoxy, for perhydropyranylmethoxy or pyridylmethoxy,

R represents hydrogen or halogen,

R ⁷ for hydrogen, hydroxy, for optionally by cyano,

Halogen, C1-C4-alkoxy, C -C4-alkyl-carbonyl or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, for each optionally substituted by halogen-substituted alkenyl or alkynyl, each with 2 to 6 carbon atoms, for each - If necessary by halogen or -CC4-substituted cycloalkyl or cycloalkylalkyl, each with 3 to 6 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally substituted by halogen alkoxy or alkenyloxy, each with up to 6 carbon atoms, or for each optionally by cyano, halogen, C _j -C4-

Alkyl, C _] -C4-haloalkyl, -C-C4-alkoxy or C _] -C4-haloalkoxy-substituted benzyl or benzyloxy, and

G represents one of the groups below,

-O-CO-, -S-CO-, -OC (R ⁸ , R ⁹ ) -CO-, -C (R ⁸ , R ⁹ ) -O-CO-, -C (R ⁸ , R ⁹ ) - C (R ⁸ , R ⁹ ) -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CO-, -C (R ⁸ ) = C (R ⁸ ) -,

C (R ⁸ ) = C (R ⁸ ) -CO-, -C (R ⁸ , R ⁹ ) -CO-, -N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CO-, - C ( R ⁸ ) = N-, -O-CO-C (R ⁸ , R ⁹ ) -

in which

Alkanediyl having 2 to 6 carbon atoms, and

R! 0 represents hydrogen or alkyl having 1 to 6 carbon atoms. Substituted aryliminoheterocycles of the general formula (I) according to claim 1, characterized in that

A represents oxygen, sulfur or the grouping NR ¹ , where

R ^{1 represents} hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl , or represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine, chlorine or bromine,

E represents one of the groupings below,

in which

Q represents oxygen, sulfur or the grouping NR ¹ (where R ^{1 has} the meaning given above as being particularly preferred) and

R represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl or t-butyl, or propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine, chlorine or bromine, and

woπn

R3 represents hydrogen, fluorine or chlorine,

R ^{4 represents} hydrogen, cyano, chlorine, bromine, methyl or trifluoromethyl,

R5 represents the grouping below,

-Ai-A ^ A ³

in which

A ^{1 stands} for a single bond, for oxygen, sulfur, -SO-, -SO ₂ -, - CO- or the grouping -NA ⁴ -, wherein A ⁴ represents hydrogen, hydroxy, methyl, ethyl, n- or i Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl, or

A ¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,

A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO -, - CO- or the grouping -NA ⁴ -, wherein A ⁴ represents hydrogen, hydroxy, methyl, ethyl, n- or i- Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propyl sulfonyl or phenylsulfonyl, or

A ² also for methylene, ethane-1, 1-diyl, ethane-1, 2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,

2-diyl or propyne

1,

3-diyl stands,

A ³ for hydrogen, hydroxyl, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, n- , i-, s- or t-butyl, n-, i-, s- or t-pentyl,

Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n- , i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i -, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphosphoryl, for propenyl, butenyl which is optionally substituted by fluorine or chlorine, Propenyloxy, butenyloxy,

Propenylamino, butenylamino, propylidene amino, butylidene amino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butinyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, each optionally with fluorine, chlorine, cyano, carboxy, methyl, ethyl, n or i-propyl,

methoxy, methoxycarbonyl or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyl oxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclo- butylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo-propyl, methoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexyl, Cyclopentylidenamino, cyclohexylideneamino, Cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxy- carbonyl or cyclohexylmethoxycarbonyl, or if appropriate by nitro, cyano, carboxy, fluorine, chlorine, bromomethyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy,

Benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (each optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl Pyrazolylmethyl, furylmethyl,

Thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy,

represents hydrogen, fluorine or chlorine,

R ⁷ for hydrogen, hydroxy, for each optionally by cyano,

Fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally with fluorine, chlorine or Bromine-substituted propenyl, butenyl, propynyl or butynyl, each optionally with fluorine, chlorine, bromine,

Methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, for each methoxy, ethoxy, n- or i-propoxy, n-, i- or or substituted by fluorine and / or chlorine s-butoxy, propenyloxy or butenyloxy, or for benzyl or benzyloxy which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, and

G represents one of the groups below, -O-CO-, -S-CO-, -OC (R ⁸ , R ⁹ ) -CO-, -C (R ⁸ , R ⁹ ) -O-CO-, -C (R ⁸ , R ⁹ ) - C (R ⁸ , R ⁹ ) -, -C (R ⁸ ) = C (R ⁸ ) -, -C (R ⁸ , R ⁹ ) -CO-, -N (R 0) -C (R ⁸ ; R ⁹ ) -CO-, -C (R ⁸ ) = N-, -O-CO-C (R ⁸ , R ⁹ ) -

in which

R ⁸ and R ^{9 are the} same or different and are individually hydrogen,

Methyl, ethyl, n- or i-propyl or together represent ethane-1,2-diyl, and

R ¹ ^ represents hydrogen, methyl, ethyl, n- or i-propyl.

4. Process for the preparation of substituted aryliminoheterocycles of the general formula (I)

R

EN ^'

_._] ^(l) ^{A _} ^ _N - AArr

in which A, E, R and Ar have the meanings given in Claim 1, characterized in that arylimino compounds of the general formula (II)

R ²

H _/ r CD

ON

I H

in which

R, R ² and Ar have the meanings given above,

- and / or tautomeric compounds for this purpose -

with reactive carbonic acid derivatives of the general formula (III) T ⁽ »D

X

in which

Q has the meaning given above and

X represents halogen, alkoxy, aryloxy or aralkoxy,

and optionally the compounds of the formulas (IA) and / or (IB) obtained in this case, in the event that R ^{2 is} hydrogen therein, with alkylating agents of the general formula (IV)

R ² -X ^J (IV)

in which

R ² has the meaning given above with the exception of hydrogen and

X ^{1 represents} halogen or the grouping -O-SO ₂ -OR ² ,

optionally in the presence of a reaction auxiliary and optionally in

In the presence of a diluent.

5. A method for controlling unwanted plants, characterized gekenn¬ characterized in that substituted aryliminoheterocycles of the general formula (I) according to claims 1 to 4 are allowed to act on plants and / or their habitat.

6. Use of substituted aryliminoheterocycles of the general formula (I) according to Claims 1 to 4 for combating undesirable plants.

7. A process for the preparation of herbicidal compositions, characterized in that substituted aryliminoheterocycles of the general formula (I) according to Claims 1 to 4 are mixed with extenders and / or surface-active agents.

8. Herbicidal agents, characterized in that they contain at least one substituted aryliminoheterocycle of the formula (I) according to Claims 1 to 4.